Customer Success Manager (AI-Enabled)

Remote (North America)

About the Opportunity

Our client is a quick-growing, venture-backed AI software company that automates the paperwork-heavy operations behind financial services. Their platform is an AI operating and decisioning system. It handles data collection, document processing, client onboarding and operational workflows, and plugs into the systems customers already use. Customers include wealth management firms, broker-dealers, insurance carriers and insurance brokers.

They're looking for a Customer Success Manager who is exceptional with AI and already uses it to work smarter every day. This suits someone who wants to help regulated, high-stakes businesses modernize how they operate.

The Role

You'll own a portfolio of customers from onboarding through renewal, acting as their strategic partner and trusted advisor. This is a hands-on role: you'll own the relationships, the outcomes and the commercial results on your book.

Importantly, you'll also help shape how the CS team works. The right person will design and share AI-assisted workflows that cut busywork, surface risk earlier and free up more time for customers.

Key Responsibilities

- Own a portfolio of mid-market and enterprise accounts from onboarding to renewal.
- Lead kickoffs, onboarding plans and time-to-value milestones for new customers.
- Run quarterly business reviews that tie product usage to customer business outcomes.
- Own renewals and drive retention,



partnering with Sales on upsell and expansion.
- Monitor account health, act early on risk signals and build save plans for at-risk accounts.
- Bring structured customer feedback to Product and Engineering.

AI-Enabled Ways of Working

- Use AI tools (ChatGPT, Claude, Gemini, Copilot or similar) daily for call prep, account research, summaries, follow-ups and QBR decks.
- Build and maintain AI-assisted workflows and automations (e.g. Zapier, Make, or native CRM and CS platform AI features).
- Create shared prompts and playbooks so the wider CS team can adopt what works.
- Apply sound judgment on data privacy, output accuracy and when a human touch matters more than automation.

What We're Looking For

- 3–5+ years in Customer Success or Account Management at a B2B SaaS company.
- A proven track record of owning renewals and hitting retention targets on a book of business.
- Hands-on experience building AI into your own workflows, with clear examples of the time saved or results delivered.
- Experience with CRM and CS platforms such as HubSpot, Salesforce, Gainsight, ChurnZero or Vitally.
- Strong communication skills and confidence presenting to senior stakeholders.
- A commercial, data-driven mindset that ties customer health to revenue outcomes.

This position reflects a current vacancy with one of our clients. Our Recruiters combine deep market expertise with AI-enabled technology to support a faster, more informed recruitment process.

📌 Customer Success Manager (Toronto)
🏢 Professional Staffing
📍 Toronto